(1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine

Base Information

• Chemical Name: (1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine
• CAS No.: 68737-65-5
• Molecular Formula: C8H18N2
• Molecular Weight: 142.244
• Hs Code.: 29213000
• European Community (EC) Number: 614-082-6,626-704-3
• DSSTox Substance ID: DTXSID20986938
• Nikkaji Number: J596.263C
• Wikidata: Q72469663
• Mol file: 68737-65-5.mol

Synonyms:trans-N,N'-dimethyl-1,2-cyclohexanediamine

Chemical Property of (1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 39-44 °C
• Refractive Index: -140 ° (C=4, CHCl3)
• Boiling Point: 186.8 °C at 760 mmHg
• PKA: 11.04±0.40(Predicted)
• Flash Point: 60.2 °C
• PSA: 24.06000
• Density: 0.895 g/cm³
• LogP: 1.51820
• Storage Temp.: 0-6°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 142.146998583
• Heavy Atom Count: 10
• Complexity: 81.3

Purity/Quality:

99% ^*data from raw suppliers

(1R,2R)-N,N''-Dimethyl-1,2-cyclohexanediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-22
• Safety Statements: 45-36/37/39-25-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1CCCCC1NC
• Isomeric SMILES: CN[C@@H]1CCCC[C@H]1NC
• Uses: (R,R)-(?)-N,N′-Dimethyl-1,2-cyclohexanediamine can be used:As a ligand in the preparation of 4H-benzo[f]imidazo[1,4]diazepin-6-one through multi-component Ullmann coupling reaction.In one of the key synthetic steps for the preparation of tricyclic γ-secretase modulators.To prepare chiral fluorous diamino-diol proligand, which is used in the synthesis of zirconium metal complexes applicable as catalysts in 1-hexene polymerization.

Technology Process of (1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine

There total 32 articles about (1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

((1R,2R)-2-Methoxycarbonylamino-cyclohexyl)-carbamic acid methyl ester (1016669-67-2) → (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane (68737-65-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Reflux; Inert atmosphere;

DOI:10.1021/ol800109s

Reference yield: 96.0%

N,N’-[(±)-trans-cyclohexane-1,2-diyl]diformamide → trans-N,N'-dimethylcyclohexane-1,2-diamine (61798-24-1,67579-81-1,68737-65-5,75599-23-4,87583-89-9,99295-66-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 65 ℃; for 16h;

DOI:10.1021/ja027433h

Reference yield: 85.0%

(1R,2R)-1,2-bis(N-methylbenzamido)cyclohexane (145615-25-4) → (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane (68737-65-5)

Guidance literature:

(1R,2R)-1,2-bis(N-methylbenzamido)cyclohexane; With hydrogenchloride; In water; for 24h; Reflux; Large scale;

With sodium hydroxide; In water; Large scale;

upstream raw materials:

(R,R)-(2-ethoxycarbonylaminocyclohexyl)carbamic acid ethyl ester

N-((1R,2R)-2-Formylamino-cyclohexyl)-formamide

dimethyl sulfate

(1R,2R)-1,2-diaminocyclohexane tartrate

Downstream raw materials:

(E)-3-[2-((3aR,7aR)-1,3-Dimethyl-octahydro-benzoimidazol-2-yl)-phenyl]-acrylic acid ethyl ester

2-((3aR,7aR)-1,3-Dimethyl-octahydro-benzoimidazol-2-yl)-benzaldehyde

<3aR-(2α,3aα,7aβ)>-2-benzyloctahydro-1,3-dimethyl-1H-1,3,2-benzodiazaphosphole 2-oxide

(3aR,7aR)-1,3-dimethyl-2-o-methoxyphenyl-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3,2-benzodiazaphosphole

Refernces

Development of a general copper-catalyzed vinylic Finkelstein reaction—application to the synthesis of the C1–C9 fragment of laingolide B

10.1016/j.tet.2016.07.018

The study presents a novel and efficient copper-catalyzed vinylic Finkelstein reaction for the synthesis of various halogenated alkenes, which are important structural elements in pharmaceuticals, agrochemicals, and natural products. The researchers developed a method to convert alkenyl iodides and bromides into their chlorinated and brominated counterparts with high yields and full retention of double bond geometry. This method's broad applicability and mild reaction conditions make it suitable for a range of functionalized substrates. The study demonstrates the potential of this reaction in total synthesis and medicinal chemistry by using it to synthesize the C1–C9 fragment of laingolide B and for the late-stage modification of drug-like molecules. The researchers also explored the extension of this halogen exchange to acetylenic and allenic Finkelstein reactions.

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